US5801244A - Sunscreens - Google Patents
Sunscreens Download PDFInfo
- Publication number
- US5801244A US5801244A US08/620,953 US62095396A US5801244A US 5801244 A US5801244 A US 5801244A US 62095396 A US62095396 A US 62095396A US 5801244 A US5801244 A US 5801244A
- Authority
- US
- United States
- Prior art keywords
- formula
- compounds
- compound
- sunscreens
- sub
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
- A61K8/4966—Triazines or their condensed derivatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
Definitions
- the present invention relates to photostabilization of synthetic polymers and the protection of human skin from sunlight radiations.
- UV radiations are noxious to human skin; in particular radiations having wavelength between 290 and 320 nm, so-called UV-B radiations, which cause erythema and sunburns, whose severity depends on the length of exposition.
- Hydrolysis can cause unwanted alterations of the cosmetic formulation, such as for example pH and/or color variations, destabilization of the formulation with formation of precipitates and/or coagulates and subsequent loss of activity and impossibility of use.
- the sunscreens, or the photostabilizing agents must have high absorption on a wide wavelength band.
- aniline derivatives of symmetric triazines not only have high absorption capacity for the ultraviolet radiations but also are highly resistant to hydrolysis.
- R and R 1 can be the same or different and are C 1 -C 18 straight or branched alkyl, C 5 -C 12 cycloalkyl optionally substituted with one or more C 1 -C 4 alkyl;
- R 2 , R 3 and R 4 can be the same or different and have the same meaning of R or are hydrogen.
- the compounds of formula (I) are useful as photostabilizing agents for synthetic polymers, these compounds are also useful as sunscreens for the protection of human skin from sunlight.
- examples of C 1 -C 18 alkyl comprise methyl, ethyl, isopropyl, t-butyl, n-hexyl, 2-ethylbutyl, 2-ethylhexyl, 1,1,3,3-tetramethylbutyl, dodecyl, hexadecyl, octadecyl.
- cycloalkyl examples include cyclohexyl, cyclopentyl, 2-, 3-, or 4-methylcyclohexyl, ter-butylcyclohexyl.
- a first group of preferred compounds are those wherein R and R 1 have the above defined meaning, R 2 is hydrogen, R 3 and R 4 have the same meaning of R and R 1 , or are hydrogen.
- a second group of preferred compounds are those wherein R 2 , R 3 , R 4 are hydrogen, R and R 1 have the above defined meaning.
- the compounds according to the present invention absorb UV radiations in a particularly intense way in the range from 290 to 320 nm. They can be then effectively used as sunscreens for the protection of synthetic polymers, of varnishes and especially in cosmetic industry for the preparation of cosmetic compositions with high Sun Protecting Factor (SPF) intended for protection of human skin from sunlight radiations.
- SPF Sun Protecting Factor
- the synthesis of the compounds of formula (I) is carried out preferably by reacting a compound of formula (II) ##STR3## with p-aminobenzamides of formula (III) and subsequently, in case when R 4 is different from R 3 , with p-aminobenzamides of formula (IIIa) ##STR4## or reacting a compound of formula (IV) ##STR5## with p-aminobenzamides of formula (V) ##STR6## where R, R 1 , R 2 , R 3 and R 4 have the above defined meanings, Z is bromine or preferably chlorine.
- the intermediates of formula (II) and (IV) are prepared according to well known processes from tribromotriazine, or preferably from trichlorotriazine and aminobenzamides of formula (V) or respectively of formula (III), for example as described in Chem. Abstr. 50, 13101 b (1956); Chem. Abstr. 54, 20061 h (1960); Chem. Abstr. 70, 37844 (1969); J. Am. Chem. Soc. 73, 2981 (1951).
- the reaction is carried out at a temperature from 50° to 200° C. in suitable organic solvents, such as for example acetonitrile, ketones as acetone, methylethyl ketone; ether as diethyl ether, diisopropyl ether, tetrahydrofuran, dioxane, aliphatic or aromatic hydrocarbons, as pentane, eptane, octane, cyclohexane, benzene, toluene, xylene or their mixtures; esters as ethyl acetate.
- the reaction can optionally be carried out in the presence of acid acceptor, such as for example alkali or alkaline-earth hydroxides, alkali metal carbonate or bicarbonates.
- p-Aminobenzamides of formula (III) and (V) can be prepared, according to well known methods, for example similarly to the method disclosed in DE 2 327 506 from p-nitrobenzoyl chloride and the corresponding amine and subsequent reduction of the p-nitro-benzamides.
- Cosmetic compositions according to the present invention containing at least a compound of formula (I), are useful for the treatment of human skin, of hairs or make-up, in decorative cosmetic, also for the protection of human skin from sunlight.
- compositions may be of different types, for example solutions, lotions, water-in-oil or oil-in-water emulsions; or also in the form of gel, lipstick, aerosol.
- compositions are prepared by formulating conventional ingredients, such as for example oils, fats, emollients, hydrating agents, moisturizing agents, softening agents, preservatives, surfactants, thickening agents, antifoam, perfumes, pigments, dyes and other else such as alcohols, polyols, electrolytes, silicone derivatives.
- solvents are triglycerides of caprinic or caprilic acid, for example castor oil, esters of fatty acids with isopropanol, propylene glycol, glycerin, propylene glycol-monomethyl or monoethyl or monobutyl ether.
- the present invention also comprises a method for protecting cosmetics from UV radiation by adding a sufficient amount of the compounds of formula (I), in this case it is the composition whose ingredients can undergo indesiderate degradation or coloring due to light to be protected from radiation induced-degradation.
- a composition may be for example hair shampoos and lacquers, hairdress lotions, hair-dye compositions, formulations for make-up, such as nail lacquers, foundation, lipstick.
- Preferred cosmetic compositions are those for the protection of human skin from sun radiations.
- a skilled person shall be able to determine the sufficient amount of compound of formula (I) to add to a cosmetic composition in order to protect it from photodegradation.
- the cosmetic compositions according to the present invention can contain one or more compounds of formula (I), in an amount comprised from 0.1 to 20%, preferably from 0.5 to 15% by weight with respect to the total weight of the composition.
- the claimed compositions can contain in combination also other sunscreens and particularly those having a maximum absorption comprised from 320 to 400 nm.
- sunscreens which can be combined with the compounds of formula (I) are for example: 3-(4-methylbenzylydene)-camphor; 2-ethylhexyl-(4-dimethylamino) benzoate, 2-ethylhexyl-4-methoxy-cinnamate, menthyl salicilate, 2-hydroxy-4-methoxy-benzophenone, 2,4,6-trianilino-(p-carbo-2-ethylhexyloxy)-1,3,5-triazine, 4-(1,1-dimethylethyl)-4-methoxydibenzoyl methane, salts of 2-phenyl-benzimidazol-5-sulfonic acid or of 2-hydroxy-4-methoxy-benzophenone-5-sulfonic acid.
- the cosmetic compositions according to the present invention may contain also inorganic pigments, commonly used in cosmetics, such as for example those used for the protection of human skin from UV radiations, for example titanium, zinc, silicon or aluminium oxides.
- polyethylene polypropylene, polystyrene, polybutadiene, polyisoprene and their copolymers, polyvinyl acetate and its copolymers, particularly with polyethylene, polyesters such as polyethylenterephthalate, polyamides such as Nylon 6 and Nylon 6,6, polyurethanes, polyacrilates, polymethacrylates, polyvinyl chloride.
- the compounds of formula (I) can be incorporated in polymers to be stabilized by means of any known method for mixing or blending additives to polymeric materials; for example, they can be mixed with the polymer in a suitable blender or mixer, or added in the form of solution or suspension in a suitable solvent such as methanol, ethanol, acetone, chloroform, then removing the solvent after mixing with the polymer, which can be in the form of powder, granulate or suspension or finally can be added to the polymer during the preparation of the same, for example in the last step of preparation.
- a suitable solvent such as methanol, ethanol, acetone, chloroform
- the compounds of formula (I) can be used also in combination with other stabilizing agents and additives generally used for polymers, such as for example phenol-based antioxydants, phosphites, hindered amines and particularly those containing in their structure the 2,2,6,6-tetramethylpiperidine group, other types of UV-Absorber based on benzotriazoles or benzophenones, plastifiers, lubricants, antistatic agents, flame retardants, titanium oxide.
- other stabilizing agents and additives generally used for polymers such as for example phenol-based antioxydants, phosphites, hindered amines and particularly those containing in their structure the 2,2,6,6-tetramethylpiperidine group, other types of UV-Absorber based on benzotriazoles or benzophenones, plastifiers, lubricants, antistatic agents, flame retardants, titanium oxide.
- the amount of compounds of formula (I) necessary to an effective stabilization of the polymer depends on different factors, such as the kind and the characteristics of the polymer, the use to which it is intended, the intensity of the radiation, the duration of exposure and the presence, if any, of other stabilizing agents.
- an amount comprised from 0.01 to 5% by weight of the polymer preferably from 0.05 to 2% is sufficient, but it is understood that a skilled technician in the field shall be able to find a suitable amount.
- the solvent was distilled off and the residue recrystallized from a mixture of toluene and octane.
- the fatty phase was warmed to 80°-90° C., the compound of Example 1 was added, then the mixture was added to water, containing the hydrosoluble compounds, heated to 80°-90° C. Warm-stirring was continued for 15-20 minutes.
- the composition was prepared as described in Example 6.
- Synthalen M was dispersed in water, then tiethanolamine, preservative, propylene glycole and ethanol mixture, wherein the compound of Example 1 was previously dissolved, was added, perfume was last added.
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Cosmetics (AREA)
- Liquid Crystal Substances (AREA)
- Glass Compositions (AREA)
- Photovoltaic Devices (AREA)
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT96MI000576A IT1283295B1 (it) | 1996-03-22 | 1996-03-22 | Filtri solari |
US08/620,953 US5801244A (en) | 1996-03-22 | 1996-03-25 | Sunscreens |
EP97103902A EP0796851A1 (fr) | 1996-03-22 | 1997-03-06 | Dérivés de s-triazine en tant qu'agent antisolaire |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
IT96MI000576A IT1283295B1 (it) | 1996-03-22 | 1996-03-22 | Filtri solari |
US08/620,953 US5801244A (en) | 1996-03-22 | 1996-03-25 | Sunscreens |
Publications (1)
Publication Number | Publication Date |
---|---|
US5801244A true US5801244A (en) | 1998-09-01 |
Family
ID=26331371
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/620,953 Expired - Lifetime US5801244A (en) | 1996-03-22 | 1996-03-25 | Sunscreens |
Country Status (3)
Country | Link |
---|---|
US (1) | US5801244A (fr) |
EP (1) | EP0796851A1 (fr) |
IT (1) | IT1283295B1 (fr) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5922122A (en) * | 1996-07-31 | 1999-07-13 | Fuji Photo Film Co., Ltd. | Pigment-dispersed composition |
US6193960B1 (en) | 1996-07-08 | 2001-02-27 | Ciba Specialty Chemicals Corporation | Triazine derivatives |
US6409999B2 (en) | 1999-07-02 | 2002-06-25 | Societe L'oreal | Synergistically UV-photoprotecting benzotriazole-substituted silicon/cinnamic acid compositions |
US6509008B1 (en) | 2001-06-26 | 2003-01-21 | L'oreal | Solubilization of 1,3,5-triazine derivatives with N-acyl amino acid esters |
US20040209880A1 (en) * | 2001-09-21 | 2004-10-21 | Timmer Richard T. | Methods and compositions of novel triazine compounds |
US20040224950A1 (en) * | 2001-09-21 | 2004-11-11 | Timmer Richard T. | Methods and compositions of novel triazine compounds |
US20050113341A1 (en) * | 2001-09-21 | 2005-05-26 | Timmer Richard T. | Medical devices employing triazine compounds and compositions thereof |
US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
US20050220728A1 (en) * | 2004-03-22 | 2005-10-06 | Mohamed Kanji | Cosmetic composition comprising a polyglycerolated silicone elastomer |
US20050227983A1 (en) * | 2004-03-24 | 2005-10-13 | Timmer Richard T | Triazine compounds and their analogs, compositions, and methods |
US20050232884A1 (en) * | 2004-04-02 | 2005-10-20 | Thomas Fondin | Method for treating hair fibers |
US20060083702A1 (en) * | 2004-04-02 | 2006-04-20 | Thomas Fondin | Hair fiber treating method |
US20060292095A1 (en) * | 2005-05-17 | 2006-12-28 | L'oreal | Gelled oil particles comprising at least one hydrophobic sunscreen |
US20070055014A1 (en) * | 2005-09-06 | 2007-03-08 | L'oreal | Cosmetic compositions containing block copolymers, tackifiers and phenylated silicones |
US20070099874A1 (en) * | 2002-09-23 | 2007-05-03 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US9675822B2 (en) | 2004-04-02 | 2017-06-13 | L'oreal | Method for treating hair fibers |
EP3275872A1 (fr) | 2016-07-29 | 2018-01-31 | 3V SIGMA S.p.A | Nouveaux composés de triazine en tant qu'agents photostabilisants |
EP3275426A1 (fr) | 2016-07-29 | 2018-01-31 | 3V SIGMA S.p.A | Compositions cosmétiques de filtres uv |
EP3578558A1 (fr) | 2018-06-05 | 2019-12-11 | 3V SIGMA S.p.A | Agents photoréactives très efficaces |
Families Citing this family (56)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19643515A1 (de) * | 1996-10-22 | 1998-04-23 | Basf Ag | Kosmetische Mittel enthaltend eine Kombination von UV-Absorbern |
DE19817296A1 (de) * | 1998-04-18 | 2000-01-20 | Beiersdorf Ag | Kosmetische oder dermatologische Zubereitungen mit einem Gehalt an unsymmetrisch substituierten Triazinderivaten, welche wasserfeste Lichtschutzzubereitungen in Form von O/W-Emulsionen darstellen |
ITMI981266A1 (it) * | 1998-06-05 | 1999-12-05 | 3V Sigma Spa | Derivati 1,3,5-trianilinotriazinici come filtri contro le radiazioni solari uv-b |
FR2779957B1 (fr) * | 1998-06-18 | 2000-08-04 | Oreal | Compositions cosmetiques photoprotectrices contenant un benzazole n-substitue, un derive de 1,3,5-triazine et un filtre organique uv-a |
FR2789579B1 (fr) | 1999-02-12 | 2002-02-01 | Oreal | Compositions cosmetiques pour la photoprotection de la peau et/ou des cheveux contenant un derive de benzotriazole et une bis-resorcinyl triazine |
US6262053B1 (en) | 1999-06-23 | 2001-07-17 | Parker Hughes Institute | Melamine derivatives as potent anti-cancer agents |
FR2799645B1 (fr) | 1999-10-13 | 2004-04-30 | Oreal | Utilisation de la dhea ou de ses precurseurs ou derives metaboliques comme depigmentant |
DE10012413A1 (de) | 2000-03-15 | 2001-09-20 | Basf Ag | Verwendung von Lichtschutzmittelkombinationen, die als wesentlichen Bestandteil 4,4'-Diarylbutadiene enthalten als photostabile UV-Filter in kosmetischen und pharmazeutischen Zubereitungen |
FR2811553B1 (fr) | 2000-07-12 | 2002-09-13 | Oreal | Compositions contenant des composes du type sel de flavylium non substitues en position 3 pour la coloration de la peau et une silicone organomodifiee |
FR2811554B1 (fr) | 2000-07-12 | 2002-09-13 | Oreal | Composition comprenant au moins un filtre uv et un sel de flavylium non substitue en position 3 pour la coloration de la peau et utilisations |
US8080257B2 (en) | 2000-12-12 | 2011-12-20 | L'oreal S.A. | Cosmetic compositions containing at least one hetero polymer and at least one film-forming silicone resin and methods of using |
FR2824266B1 (fr) | 2001-05-04 | 2005-11-18 | Oreal | Composition cosmetique de soin ou de maquillage des matieres keratiniques comprenant un ester a groupement aromatique et un agent photoprotecteur et utilisations |
EP1302199A3 (fr) | 2001-10-16 | 2004-07-28 | L'oreal | Compositions pour la coloration de la peau proche du bronzage naturel a base d'un pigment du type monascus et utilisations |
FR2833164B1 (fr) | 2001-12-07 | 2004-07-16 | Oreal | Compositions cosmetiques antisolaires a base d'un melange synergique de filtres et utilisations |
US20050008598A1 (en) | 2003-07-11 | 2005-01-13 | Shaoxiang Lu | Cosmetic compositions comprising a structuring agent, silicone powder and swelling agent |
US6958155B2 (en) | 2002-06-12 | 2005-10-25 | L'oreal | Cosmetic compositions comprising at least one polysiloxane based polyamide |
FR2872417B1 (fr) | 2004-07-02 | 2007-06-08 | Oreal | Compositions contenant un derive de triazine et un derive arylalkyl benzoate; utilisations en cosmetique |
US8158136B2 (en) | 2004-08-18 | 2012-04-17 | L'oréal | Emulsification system for use in cosmetics |
EP1676556B1 (fr) | 2004-10-22 | 2012-01-11 | L'Oréal | Composition cosmétique contenant un polymère de polyorganosiloxane |
EP1661549A1 (fr) | 2004-11-04 | 2006-05-31 | L'oreal | Compositions cosmétiques et méthodes d'utilisation |
US20060127331A1 (en) | 2004-11-04 | 2006-06-15 | L'oreal | Moisturizing compositions |
FR2879447B1 (fr) | 2004-12-17 | 2007-01-26 | Oreal | Procede cosmetique de soin de la peau et kit associe |
FR2879456B1 (fr) | 2004-12-20 | 2007-05-04 | Oreal | Composition solaire comprenant au moins un filtre uv lipophile et au moins une hydroxyalkyluree |
FR2883168B1 (fr) | 2005-03-18 | 2008-01-11 | Oreal | Compositions cosmetiques de soin, renforcement et/ou reparation des substrats keratiniques comprenant des polypeptides kap |
US8216554B2 (en) | 2005-04-20 | 2012-07-10 | L'oreal | Stable transfer-resistant self-tanning gel containing a water-soluble or water-dispersible gelling agent |
US9180321B2 (en) | 2005-07-13 | 2015-11-10 | L'oreal S.A. | Cosmetic compositions containing liposoluble polymers and tackifiers |
ES2264904B1 (es) * | 2005-07-13 | 2007-12-01 | Isdin, S.A. | Nuevos derivados de heptaazafenaleno, procedimientos para su obtencion, asi como utilizacion de estos como agentes protectores contra la radiacion uv. |
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FR2909552B1 (fr) | 2006-12-12 | 2009-11-20 | Oreal | Utilisation cosmetique de l'acide anisique pour favoriser la desquamation |
FR2918879B1 (fr) | 2007-07-20 | 2009-10-16 | Oreal | Emulsion huile-dans-eau contenant un polymere amphiphile. |
DE102007035567A1 (de) | 2007-07-26 | 2009-01-29 | Basf Se | UV-Filter-Kapsel |
EP2100585A1 (fr) | 2008-03-11 | 2009-09-16 | L'Oréal | Composition cosmétique comprenant un composé d'acide ascorbique ou d'acide salicylique |
FR2938191B1 (fr) | 2008-11-07 | 2011-01-14 | Oreal | Emulsion huile-dans-eau contenant un polymere amphiphile et un elastomere silicone |
FR2939042B1 (fr) | 2008-11-28 | 2010-11-26 | Oreal | PROCEDE DE DEPIGMENTATION DES MATIERES KERATINIQUES A l'AIDE DE COMPOSES DITHIOLANNES. |
EP2210887A1 (fr) | 2009-01-14 | 2010-07-28 | Isdin, S.A. | Dérivés de bis-résorcinyl triazine en tant qu'agents de protection contre le rayonnement UV |
FR2949330B1 (fr) | 2009-08-28 | 2012-08-10 | Oreal | Composition cosmetique comprenant un derive diphenyl-methane hydroxyle |
BR112012004218B1 (pt) | 2009-08-28 | 2021-12-07 | L'oreal | Composição e processo de fotoestabilização |
JP2011074070A (ja) | 2009-09-07 | 2011-04-14 | Fujifilm Corp | 紫外線吸収性組成物 |
DE102009044891A1 (de) | 2009-12-14 | 2011-06-16 | Gabriele Dr. Blume | Trägersystem zum Einschließen lipophiler Wirkstoffe und Öle in hoher Konzentration |
FR2968661B1 (fr) | 2010-12-14 | 2016-01-01 | Oreal | Procede de depigmentation des matieres keratiniques a l'aide de composes thiopyridinones |
FR2969149B1 (fr) | 2010-12-16 | 2012-12-28 | Oreal | Procede de depigmentation des matieres keratiniques a l' aide de composes derives de resorcinol |
US9855207B2 (en) | 2011-01-28 | 2018-01-02 | Momentive Performance Materials Gmbh | UV-photo-protecting cosmetic composition |
FR2991984B1 (fr) | 2012-06-19 | 2014-07-11 | Oreal | Nouveaux derives de resorcinol et leur application cosmetique |
FR2991985B1 (fr) | 2012-06-19 | 2019-11-08 | L'oreal | Procede de depigmentation des matieres keratiniques a l'aide de nouveaux composes derives de resorcinol |
FR2991986B1 (fr) | 2012-06-19 | 2015-02-27 | Oreal | Nouveaux derives de resorcinol et leurs applications cosmetiques |
BR112015017289B1 (pt) | 2013-01-21 | 2020-03-10 | L'oreal | Composição cosmética, processos cosméticos não terapêuticos para cuidado e/ou maquilagem de uma matéria queratínica, para limitar o escurecimento da pele e para prevenir e/ou tratar os sinais de envelhecimento e usos de uma composição cosmética |
FR3045604B1 (fr) | 2015-12-18 | 2018-01-26 | L'oreal | Procede de depigmentation des matieres keratiniques a l'aide de composes thiopyridinones |
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FR3117789A1 (fr) | 2020-12-22 | 2022-06-24 | L'oreal | Composition cosmétique comprenant au moins une argile, au moins un corps gras cristallisable et au moins un filtre UV liposoluble |
WO2024089231A1 (fr) | 2022-10-28 | 2024-05-02 | Dsm Ip Assets B.V. | Compositions d'écran solaire comprenant un oligosaccharide de lait maternel |
FR3141345A1 (fr) | 2022-10-28 | 2024-05-03 | L'oreal | Emulsion comprenant une dispersion polymérique spécifique et un filtre UV |
WO2024089235A1 (fr) | 2022-10-28 | 2024-05-02 | Dsm Ip Assets B.V. | Composition d'écran solaire comprenant un oligosaccharide de lait humain |
WO2024089234A1 (fr) | 2022-10-28 | 2024-05-02 | Dsm Ip Assets B.V. | Composition d'écran solaire comprenant un oligosaccharide de lait humain |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2328961A (en) * | 1942-09-01 | 1943-09-07 | Gen Electric | Triazine derivatives |
US3697520A (en) * | 1970-04-30 | 1972-10-10 | Ciba Geigy Ag | Triazine carboxylic acids and esters |
EP0517104A1 (fr) * | 1991-06-04 | 1992-12-09 | 3V SIGMA S.p.A | Dérivés de 1,3,5-triazines, leur préparation et leur utilisation comme filtres solaires |
EP0570838A1 (fr) * | 1992-05-19 | 1993-11-24 | 3V SIGMA S.p.A | Dérivés de 1-triazine comme stabilisateurs à la lumière |
-
1996
- 1996-03-22 IT IT96MI000576A patent/IT1283295B1/it active IP Right Grant
- 1996-03-25 US US08/620,953 patent/US5801244A/en not_active Expired - Lifetime
-
1997
- 1997-03-06 EP EP97103902A patent/EP0796851A1/fr not_active Withdrawn
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Cited By (31)
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US6193960B1 (en) | 1996-07-08 | 2001-02-27 | Ciba Specialty Chemicals Corporation | Triazine derivatives |
US5922122A (en) * | 1996-07-31 | 1999-07-13 | Fuji Photo Film Co., Ltd. | Pigment-dispersed composition |
US6409999B2 (en) | 1999-07-02 | 2002-06-25 | Societe L'oreal | Synergistically UV-photoprotecting benzotriazole-substituted silicon/cinnamic acid compositions |
US6906067B2 (en) * | 1999-12-28 | 2005-06-14 | Bristol-Myers Squibb Company | N-heterocyclic inhibitors of TNF-α expression |
US20050239770A1 (en) * | 1999-12-28 | 2005-10-27 | Moriarty Kevin J | N-heterocyclic inhibitors of TNF-alpha expression |
US7479495B2 (en) * | 1999-12-28 | 2009-01-20 | Pharmacopeia, Inc. | N-heterocyclic inhibitors of TNF-α expression |
US6509008B1 (en) | 2001-06-26 | 2003-01-21 | L'oreal | Solubilization of 1,3,5-triazine derivatives with N-acyl amino acid esters |
US20040209880A1 (en) * | 2001-09-21 | 2004-10-21 | Timmer Richard T. | Methods and compositions of novel triazine compounds |
US20050113341A1 (en) * | 2001-09-21 | 2005-05-26 | Timmer Richard T. | Medical devices employing triazine compounds and compositions thereof |
US20040224950A1 (en) * | 2001-09-21 | 2004-11-11 | Timmer Richard T. | Methods and compositions of novel triazine compounds |
US7132423B2 (en) | 2001-09-21 | 2006-11-07 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US20070004729A1 (en) * | 2001-09-21 | 2007-01-04 | Timmer Richard T | Methods and compositions of novel triazine compounds |
US7169784B2 (en) | 2001-09-21 | 2007-01-30 | Reddy Us Therapeutics, Inc. | Medical devices employing triazine compounds and compositions thereof |
US7268134B2 (en) | 2001-09-21 | 2007-09-11 | Reddy Us Therapeutics, Inc. | Medical devices employing triazine compounds and compositions thereof |
US20070099874A1 (en) * | 2002-09-23 | 2007-05-03 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7332489B2 (en) | 2002-09-23 | 2008-02-19 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US20050220728A1 (en) * | 2004-03-22 | 2005-10-06 | Mohamed Kanji | Cosmetic composition comprising a polyglycerolated silicone elastomer |
US7378103B2 (en) | 2004-03-22 | 2008-05-27 | L'oreal | Cosmetic composition comprising a polyglycerolated silicone elastomer |
US7335770B2 (en) | 2004-03-24 | 2008-02-26 | Reddy U5 Therapeutics, Inc. | Triazine compounds and their analogs, compositions, and methods |
US20050227983A1 (en) * | 2004-03-24 | 2005-10-13 | Timmer Richard T | Triazine compounds and their analogs, compositions, and methods |
US20060083702A1 (en) * | 2004-04-02 | 2006-04-20 | Thomas Fondin | Hair fiber treating method |
US20050232884A1 (en) * | 2004-04-02 | 2005-10-20 | Thomas Fondin | Method for treating hair fibers |
US7976831B2 (en) | 2004-04-02 | 2011-07-12 | L'oreal S.A. | Method for treating hair fibers |
US9675822B2 (en) | 2004-04-02 | 2017-06-13 | L'oreal | Method for treating hair fibers |
US10702464B2 (en) | 2004-04-02 | 2020-07-07 | L'oreal | Method for treating hair fibers |
US20060292095A1 (en) * | 2005-05-17 | 2006-12-28 | L'oreal | Gelled oil particles comprising at least one hydrophobic sunscreen |
US20070055014A1 (en) * | 2005-09-06 | 2007-03-08 | L'oreal | Cosmetic compositions containing block copolymers, tackifiers and phenylated silicones |
US7884158B2 (en) | 2005-09-06 | 2011-02-08 | L'Oré´al | Cosmetic compositions containing block copolymers, tackifiers and phenylated silicones |
EP3275872A1 (fr) | 2016-07-29 | 2018-01-31 | 3V SIGMA S.p.A | Nouveaux composés de triazine en tant qu'agents photostabilisants |
EP3275426A1 (fr) | 2016-07-29 | 2018-01-31 | 3V SIGMA S.p.A | Compositions cosmétiques de filtres uv |
EP3578558A1 (fr) | 2018-06-05 | 2019-12-11 | 3V SIGMA S.p.A | Agents photoréactives très efficaces |
Also Published As
Publication number | Publication date |
---|---|
EP0796851A1 (fr) | 1997-09-24 |
ITMI960576A1 (it) | 1997-09-22 |
IT1283295B1 (it) | 1998-04-16 |
ITMI960576A0 (fr) | 1996-03-22 |
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